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Giving up the security of a full-time job to start
your own business is a risky, often stressful move. "The
biggest reason people don't end up quitting is the fear of
uncertainty. They don't know what might happen and they don't
want to give up the security that they already have," says Sean
Ogle, who quit a job in finance to live in Thailand and run a
virtual search engine optimization and Web consultancy.

How do you know when the time is right to make the leap? Here are
10
questions to ask before you quit your job.

Are you just miserable in your current
job?
Some people who think they want to be entrepreneurs are just
unhappy in their current roles, says Pamela Slim, the Mesa,
Ariz.-based author of Escape from Cubicle Nation
(Penguin, 2010). Developing a thorough business
plan can help you avoid any impulsive decisions. "In addition
to wanting to quit, you have to have a viable business idea and
an effective marketing and operations plan," she says. As you
work on your plan, she advises, keep your job and income as long
as possible.

What will your new day-to-day routine be
like?
Instant freedom can be dangerous. Ogle recommends developing a
daily schedule to follow, just as you did in your 9-to-5 job.
"When you now have all of this free time it gets really easy to
say, 'Oh, I'll do that later'," he says. The week after quitting
his job, Ogle started going to the gym at the same time he would
have arrived at his old office each morning. And after the gym,
he worked the same hours that he did for his former employer.

How will you raise money to keep the business
going?
Lack of capital is one of the main hurdles to entrepreneurship.
Rather than figuring out cash flow as you go along, it's best to
come up with realistic projections as part of your business plan
before deciding whether you can afford to leave your job. Your
business may not be profitable for three to five years, so it's
important to be realistic about how you'll support yourself
financially, says Sharon Lechter, author of Three Feet From
Gold: Turn Your Obstacles Into Opportunities (Sterling
Publishing, 2009) and a financial literacy expert in Phoenix.
Anticipating your financial needs "allows you to focus your
energy on building your new business rather than worrying how you
are going to pay the bills," she says.

Have you factored in possible unforeseen
costs?
When Jody Dyer launched Blackbird Tees, an apparel company in
Richmond, Va., she was surprised by the many expenses her
business plan hadn't anticipated. We spent "thousands of dollars
experimenting with different fabric styles and inks, messing up
screens, destroying shirts, making the wrong color choices," says
Dyer, who sells her products on Etsy. "At the time, those errors
were financially crippling." Rather than going out of business,
Dyer fell back on freelance copywriting gigs to make ends meet.
"Supplementing your income through freelance or part-time work
can alleviate some of that strain," she says.

Are you willing to take on multiple roles?
Starting a business means you'll be wearing many hats. "One day
you are the tech person, one day you are the salesperson, one day
you are the cleaning person," says Shobha Tummala, founder of an
eponymous chain of beauty salons in New York City. "You can't
have an ego." So before leaving your job, you need to decide if
you will be happy performing a variety of functions, from
marketing to maintenance.

What are your strengths and weaknesses?
As you consider the multiple roles, be honest with yourself about
what you're best at and where you need to improve, Tummala
advises. Perhaps you need to beef up your programming skills or
understanding of finance--or find a partner with a complementary
skill set. If you don't have a way to overcome your weaknesses,
it may be best to stay in your current role.

Who are your future customers--and
competitors?While you may not be able to thoroughly test
the market potential for your business concept, you should at
least understand who your likely customers are and what kind of
competition you would face. If you're not quite sure, consider
pursuing your idea part-time, suggests Ellen Rohr, president of
Bare Bones Biz, a small-business consultancy in Rogersville, Mo.
"You can test your plan and adjust it in a soft launch before you
sink too much into an unprofitable venture."

Is your support network on board?
To help ease the transition, you should share your
entrepreneurial plans with family members and see if they support
the tradeoffs involved in starting a business. Be quite explicit
about the risks, Slim says. "When one person goes into business,
everyone in the family unit is affected." If your partner and
other members of your support network are reluctant to back your
idea, you may want to rethink quitting your current job.

Do you have a backup option?
Developing a plan B before going off on your own will help you
avoid getting blindsided. Is there something you can do part-time
if you need to temporarily bring in money, or will you need to
seek new full-time employment and put your plans on hold? To keep
your options open, stay in contact with recruiters, previous
employers and other networking contacts.

How will you avoid burning bridges?
If you decide to quit, remember that your employer could be
helpful to you as you launch your new venture. Rather than resign
abruptly, figure out a way to leave in good standing. Give plenty
of notice to help your employer handle the transition. And be
open about your future entrepreneurial plans, Ogle says. "Usually
[companies] will understand it, and even offer to help out
however they can." Employers can assist by giving you flexible
time off or retaining your services as a consultant.